Five Times Dean Sees
by Becomingwhaturmeantobe
Summary: Dean sees his future five different times with the help of someone unexpected.


**Author's Note:** Thanks so much to **rue37** or **twasadark** for an awesome beta job and for helping me out with this. Any mistakes in here are mine. This is an AU. It's probably going to be confusing but I didn't know where else to start. This is probably going to be the beginning of a new 'verse I want to start. Feedback welcome!

**1.**

He's bored out of his freaking mind at the library, flipping through some dusty old book on the history of Greensboro, when he sees her. Dad's off talking to the lady whose house is being haunted by a poltergeist with a penchant for opening silverware drawers and flinging knives around, leaving Dean behind to do the dirty work. Dirty work, which Sam used to do before he ran off to college and left Dean behind.

Movement out of the corner of his eye catches his attention and he looks up to see a little girl, maybe 10 years old, with a straggly ponytail and freckled cheeks, staring at him from a few feet away. She gives him a shy smile, and he thinks she looks familiar. From where he's not sure. He smiles back, and adds a little wave, which she returns, and then he looks back down at the book to see that he's paused on the very page where a picture of the haunted house appears. Strange.

He reads through the section on the house and then starts to write down the things he was looking for in the spiral notebook at his side. He pauses mid-write as he gets the eerie feeling of being watched. When he looks up the little girl is still standing there, what for he has no idea. She's just staring at him, not moving at all, with a small smile playing on her face.

He blinks and looks behind him. Maybe she was looking at someone else? No one's behind him and when he turns back around she's gone.

He emerges from the library an hour later and meets Dad back at the house. "Got anything?" Dad asks.

Dean tells him what little he found. It's all-important though and it turns out that the poltergeist is just an angry caretaker who used to live on the land behind the house.

"Mrs. Moore will be happy," Dad says as they load the guns with rock salt and get the gasoline and salt in the car.

They finish the job within an hour. Mrs. Moore invites them for tea. Dean's never been to the woman's house and Dad's never been inside, so it makes sense that they've never met her granddaughter before.

Jessica Moore is blonde and tall. She's just his type. He'd love to get her alone after this is all done. She smiles politely, he grins back, and thanks them before giving some excuse about wanting to go back to her room and study before he can even attempt to talk to her.

"She just wants to talk to her boyfriend." Mrs. Moore "Call me Grace," confided in them. "Nice boy, wish he came to stay with us over the break."

Dean wants to get out of there as soon as possible. Any ideas about after having been forgotten at the idea that she already was taken, the chick obviously wasn't into him. But Grace wants them to stay for dinner. "It's the least I can do. You saved our lives. A home cooked meal will be good for you!"

So they stay. It's awkward at first. Jessica sits next to her grandmother, across from Dad and Dean and they're silent.

"How's the studying, Jess?" Her grandmother asks, waggling her eyebrows at both Dean and his father.

"Good," Jessica answers before taking a sip of her drink.

"Why don't you tell John and Dean what you're studying?" Grace says.

"Oh, it's nothing-"

"She's studying to be a doctor!" Grace smiles proudly. "At Stanford!"

Dean nearly coughs on his drink at that, but manages to swallow it down.

"You must be very proud," Dad says.

"Oh we are!" She tilts her head. "Didn't you say your son was away at college?"

John smiles a bit. "Yes."

"Where's that?" Grace asks.

"Stanford."

Grace thinks that's funny. "What a coincidence! Jessi, dear maybe you know the boy?"

Jess nods. "What's his name?"

"Sam Winchester." Dean answers and it's Jess's time to cough.

"You're Dean?" She asks when she swallows.

Dean nods. "Yeah?"

Grace is laughing again. "Sam is Jessi's boyfriend!"

**2.**

Dad's been missing for two weeks with nothing but a voicemail to let him know that he's okay when he sees her again. He only recognizes her because she's familiar like he saw her once years ago, but couldn't recall when. He doesn't know who she is but she's standing outside his car after he just called Dad for the four billionth time. She smiles at him like before and just looks at him. He doesn't know why he's seeing her but he now knows that she's not some random little girl. He surveys her for a minute. She has wavy light brown hair and deep green eyes. Her smile is familiar but he can't remember from where. She's wearing a dress like a shirt with jeans under it that looked ripped. He's about to get out of the car and walk over to her when she gives another small wave and then disappears.

He leans back against the seat and closes his eyes tightly.

In the next hour he's on his way to California.

**3.**

He thought he had at least a couple years of space between seeing her again not forty-eight hours. But she's there just as he's getting out of the car to go up to Sam's apartment. This time he ignores her and walks up to the door and pushing it open, but every time he turns the corner she's there.

He looks around quickly right before he decides the window is probably a better bet and she's still there. She even follows him into the alley and up the fire escape and when he turns around before going inside she's gone.

He walks around the apartment and notices Sammy still puts the salt line up. He makes his way around the apartment and into what he thinks must be the living room, when someone attacks him.

"Easy there, tiger." He grins at Sammy when he pins him to the ground.

His little brother looks surprised. "Dean? You scared the crap out of me!"

Dean smirks. "That's cause you're out of practice."

Sam pins Dean under him. "Or not," Dean says. "Get off me."

Sam pulls him up. "Dean, what the hell are you doing here?"

"Well, I was looking for a beer," he says although isn't that the truth.

"What the hell are you doing here?" Sam repeats.

Dean gives. "Okay, alright, we have to talk."

"Uh, the phone?"

"If I'd have called, would you have picked up?"

Before Sam can answer the lights come on. "Sam?"

Dean turns to see Jessica standing by the door. "Jess, hey. Dean this is my girlfriend, Jessica."

Dean grins at her. "We've met."

Sam raises his eyebrows. "Huh?"

Jess bites her lip. And Dean goes to try to explain, he had a few interesting comments in mind but Jess starts talking before him. "Your Dad and Dean helped my grandma with a poltergeist problem a year ago." She walks over to him. "I'm sorry I didn't tell you, I just figured that if you didn't want me to know I probably shouldn't pry."

Dean nods. "Smart girl."

Sam blows out his breath. "No, no, it's okay. I'm just shocked."

Jess places a hand on Sam's shoulder before turning to Dean. "Where is your dad?"

Dean turns back to Sam. "That's kind of what I have to talk to you about."

Sam nods. "Yeah?"

"Dad's gone, he went on a-" He paused. "Hunting trip and he hasn't been home in a few days."

"I'm sure he'll stumble in after a while."

Dean rolls his eyes. "Yeah well, he's been gone for a few weeks. He was working some two-lane blacktop outside of Jericho, California."

Sam raises his eyebrows. "Where were you?"

Dean grins. "Working a job in New Orleans."

"Dad let you hunt by yourself?"

"I'm twenty-six, dude."

Sam suddenly looked over at Jess. "I'm sorry. Why don't you go back to sleep? We'll go outside."

It was Jess's turn to roll her eyes. "I'm okay."

Dean smiles at her. "Kind of have to agree with your boyfriend. Got something to show him outside. We'll be right back."

Sam nods. "I'll be right back."

Sam follows Dean down the stairs of the building and out the door.

"Look man," Dean says when they get outside. "Dad's missing. I need your help."

"I can't just leave, Dean," Sam says, shocked that his brother is asking for help. "You can do it by yourself."

"No I can't." Dean adds.

"Yes you can."

"Yeah, well I don't want too." He adds, looking defeated.

Sam shook his head. "What exactly was it, in Jericho?"

Dean opens the trunk and grabs a couple of papers and hands them to Sam. "About a month ago a guy went missing. They found his car but he'd vanished. Completely MIA."

"Maybe he was kidnapped?" Sam asked looking at one of the articles.

"Yeah, well. Here's one in April. Another one in December, '04, '03, '98, '92. Ten of them over the past twenty years. All men and all in the same five mile stretch of highway. So Dad started to go dig around. That was three weeks ago. I haven't heard from him since, which is bad enough and then I get this."

Dean searches around for the tape player with the recording of the voice message. He plays the one with his Dad and then the one with the girl's voice.

"You know there's EVP on that?" Sam points out after the recording is done.

Dean grins. "Kind of like riding a bike, isn't it?

"I have to be back by Monday." Sam says and Dean smiles and knows he's won. "First thing Monday." He adds.

"What's first thing Monday?"

"Law school interview."

Dean raises an eyebrow. "Law school?"

"Yeah, my whole future on a plate."

Dean rolls his eyes and mutters something about law school.

They go back upstairs and Jess is waiting by the door. "You okay?" She asks.

Sam nods and Jess follows Sam back into their room. When they come back, two bags are packed.

"You need all that, Sammy? Geez, you are a freaking girl."

"It's not all for me," Sam grumbles.

Dean looks at Jessica. "She's coming?"

Jess nods. "I want to help you find your dad."

Dean grins and lets Jess leave the apartment. He pulls Sam aside before they head downstairs. "Sam? Marry that girl."

Just as Dean starts the Impala he sees the little girl again. This time she's grinning. He smiles at her in return, not knowing who she was, but somehow knowing, like a gut instinct, she was alright.

**4.**

He's in a small town in Indiana on a small hunt that gets finished fast. Sam decided to take the girls on vacation to NYC and meets Dean for the hunt. After they're done Dean tells Sam to go back to his family with a promise he'll meet with them in a day or two. Dean decides to spend the rest of his time elsewhere. He went to Indiana once a few years back for this whole road trip thing. And he met a chick there named Lisa Braeden who just happened to live in a nearby town next to the town where they were in. Talk about coincidences.

It's been about seven years since he last saw her and she moved from the small apartment to a nice house in suburbia. He gets out of the car and walks up the driveway. The little girl is standing on the lawn grinning at him again when he goes past. He raises his eyebrows at her, but this time she giggles before disappearing.

He rings the doorbell and Lisa answers within seconds.

"Dean?" She says, like she's not sure he's real.

"Lisa." He smiles.

She smiles back. "What are you doing here?"

"I was around and I decided to stop by. I remember you love surprises."

She's plenty surprised and she laughs. "Yeah, I do. But I'm having a party."

"A party? I love parties."

She grins at him and invites him inside.

"My son Ben is turning seven today," She said and pointed him out among a sea of partygoers surrounding the cake and a freckled light brown haired boy.

"Seven?" He asks. Seven years ago he met her.

She smiles. "Mmhmm."

"Oh."

**5.**

He's standing in the maternity wing of the hospital staring at the babies behind the glass. He can pick her out from all the rest. Babies definitely do not look all the same because she is gorgeous. He stares at her, his little girl, at her ten fingers and ten toes, at the bear in the corner and at the name, Madison Alyssa Winchester.

He feels someone brush against him and looks down. There she is again, this little girl who's been following him around for the past few years. She smiles at him and peers up over the glass. He knows who she is now.

"Hi, Daddy!" She says like she knows he's figured out.

He laughs at that and smiles when she disappears. "See you later alligator,"

"Dad!" Another voice says from down the hallway. Ben is walking as fast as he can, in a slow jog toward Dean, Sam and his girls behind him. Ben jumps into his arm, because of all the things he's getting to big for that isn't one of them and points at his little sister. "That's her?"

"Yep, buddy. That's your sister."

"She's pretty," says 4-year old Mary, who is standing on her tippy-toes beside her Uncle Dean and Daddy.

"You alright, dude?" Sam asks, before squeezing his shoulder tight.

Dean laughs. "Yeah."

"Baby?" Mikayla asks.

"Yeah, honey, Uncle Dean's baby. That's Maddy."

"Ma-dee?" Mikayla sounds it out and giggles. "Baby?"

Sam gives her a raspberry on the cheek and shifts her to the other side. "She's beautiful, Dean."

Dean grins at his brother. "Yeah, she is."

He never told anyone about the fact that he saw his daughter years before she was born. But one day when she's older they'll sit down and have a chat and Maddy will point out that she's seen things before, certain things she can't possibly have known or seen. And only Dean will know that she's seen the past while he saw the future.


End file.
